WO2000003597A1 - Herbicides a phenylsulfonylurees substituees pour lutter contre les mauvaises herbes chez le riz - Google Patents

Herbicides a phenylsulfonylurees substituees pour lutter contre les mauvaises herbes chez le riz Download PDF

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Publication number
WO2000003597A1
WO2000003597A1 PCT/EP1999/004881 EP9904881W WO0003597A1 WO 2000003597 A1 WO2000003597 A1 WO 2000003597A1 EP 9904881 W EP9904881 W EP 9904881W WO 0003597 A1 WO0003597 A1 WO 0003597A1
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Prior art keywords
alkyl
fenoxaprop
group
compounds
herbicides
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PCT/EP1999/004881
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German (de)
English (en)
Inventor
Erwin Hacker
Hermann Bieringer
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Aventis Cropscience Gmbh
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Application filed by Aventis Cropscience Gmbh filed Critical Aventis Cropscience Gmbh
Priority to MXPA01000572 priority Critical patent/MX224001B/es
Priority to KR20017000608A priority patent/KR100676019B1/ko
Priority to EP99936516A priority patent/EP1096855B1/fr
Priority to PL345665A priority patent/PL198867B1/pl
Priority to UA2001021086A priority patent/UA70954C2/uk
Priority to CA2337521A priority patent/CA2337521C/fr
Priority to AU51587/99A priority patent/AU769790B2/en
Priority to BRPI9912829-2A priority patent/BR9912829B1/pt
Priority to CN998102016A priority patent/CN1314785B/zh
Priority to HU0104456A priority patent/HU229832B1/hu
Priority to DE59911002T priority patent/DE59911002D1/de
Priority to JP2000559741A priority patent/JP4621353B2/ja
Priority to IL14076599A priority patent/IL140765A0/xx
Priority to AT99936516T priority patent/ATE281077T1/de
Priority to SK52-2001A priority patent/SK286315B6/sk
Publication of WO2000003597A1 publication Critical patent/WO2000003597A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/76—1,3-Oxazoles; Hydrogenated 1,3-oxazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/36—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof

Definitions

  • the invention relates to the technical field of plant protection products, in particular the invention relates to herbicidal compositions containing compounds of the formula I.
  • R 2 is I, or CH 2 NHS0 2 CH 3 ;
  • R 3 is methyl or methoxy; and ZN or CH; and / or their salts, which are outstandingly suitable for controlling weeds in rice which have hitherto been difficult to control with individual herbicides, in particular grass-like, dicotyledonous and / or cyperaceae-like weeds in rice or transgenic rice cultures.
  • Dl discloses iodinated arylsulfonylureas of the general formula 1 and their salts
  • Phenylsulfonylureas of the general formula 2 and their salts are known from E2,
  • D3 discloses herbicidal compositions comprising A) at least one herbicidal active ingredient from the group of the substituted phenylsulfonylureas of the general formula 3
  • Sulfonylureas according to WO 94/10154, flupyrsulfuron (DPX-KE459), sulfosulfuron (MON37500), KIH-2023, glufosinate, glufosinate-P or glyphosate are known.
  • the aas of Dl and D2 according to general formulas 1 and 2 known sulfonylureas for the most part have one useful to good effectiveness against a wide range of economically important mono- and dicotyledonous harmful plants on and also under the specific crop conditions weeds occurring in rice, such as. B. Sagitta ⁇ a, Alisma, Eleocharis, Scirpus, Cyperus etc., are fought with the help of active ingredients of the general formulas 1, 2 and 3, for optimal control of the spectrum occurring in agricultural practice, especially in rice, rich in monocotyledonous and ⁇ icotyledonous weeds however, the individual active ingredients are often not sufficient.
  • the synergistic combinations of the D3 or the D4 cannot generally be used in rice with above-average success. At least this could not be expected with a high degree of probability.
  • the useful plant rice is damaged to a not inconsiderable degree by most of the combinations known from D3 or D4, so that these are not suitable for use in rice crops.
  • Eleocharis spp. For example Eleocharis kuroguwai, Cyperus serotinus, Scirpus juncoides, but also other predominantly ⁇ germinate from perennial organs in the Bode and can be characterized combated difficult than weeds which germinate from seeds of weeds, and also environmentallyolattrige species listed in the weeds are not easily controllable in an optimal manner across the entire spectrum of weeds.
  • herbicidal compositions having the features of claim 1.
  • the invention thus relates to herbicidal compositions comprising
  • At least one herbicidal active ingredient from the group of substituted phenylsulfonylureas of the general formula I and their agriculturally accepted, i.e. acceptable salts
  • R, 2 I or CH 2 NHS0 2 CH 3 means; RR 33 MMeetthhyyll ooddeerr MMeethoxy means; and
  • Bc selectively in rice, herbicides active primarily against cyperaceae and Bd) selectively in rice, mainly herbicides active against grasses and dicotyledonous plants and cyperaceae harmful plants,
  • R 1 (-CC 8 ) alkyl, (C3-C4) -alkenyl, (C3-C4) -alkynyl or (C1-C 4 ) -alkyl, which is one to four times by radicals from the group halogen and (C ⁇ ⁇ C 2 ) alkoxy is substituted in combination with
  • R 1 is (C1-C4) alkyl
  • R is : (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkylthio or (CC 4 ) alkoxy, each of which may be substituted by one or more halogen atoms, or
  • R is hydrogen or halogen
  • R “" is hydrogen or (C 1 -C 4 ) alkyl
  • R 10 is hydrogen, halogen, cyano, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) -alkylthio or -NR R 12 ,
  • R -7 and R 8 are the same or different hydrogen or
  • R 10 is hydrogen or (C 1 -C 4 ) alkyl, the latter optionally being substituted by one or more halogen atoms, and R 11 u.
  • R 12 is the same or different hydrogen, (C ⁇ ⁇
  • R 1 (-C 8 ) alkyl, (C 3 -C4) alkenyl, (C 3 -C 4 ) alkynyl or (C 1 -C4) alkyl, the one to four times by radicals from the group halogen and (-C ⁇ C 2 ) alkoxy is substituted, means m combination with
  • Oxyfluorfen or metsulfuron are the only herbicidal active ingredients
  • the combinations of herbicidal active ingredients of types A and B according to the invention make it particularly advantageous to achieve the control of the weed spectrum required by the practitioner, and individual species which are difficult to control are also detected.
  • the combinations of active ingredients of the individual combination partners contained in the combination can be significantly reduced with the combinations according to the invention, which allows more economical solutions on the part of the users.
  • boundary conditions l) and n) (disclaimer regarding product protection) take into account previously known combinations, although these previously published combinations do not allow any conclusions to be drawn about the suitability of the combined preparations in rice applications.
  • disclaimer 1 avoids the combinations of one or more type A compounds and a type B connection already known from the D3, their field of application clearly differing from the use of the combinations according to the present invention and the subjects of the D3 and the invention are thus clearly differentiated from one another. While D3 describes combinations with herbicides for use in cereals or corn, the present invention relates to combinations for use in rice.
  • the compounds of type A can form salts in which the hydrogen of the -SO 2 ⁇ NH group is replaced by a cation suitable for agriculture.
  • These salts are, for example, metal, in particular alkali metal salts (for example Na or K salts) or alkaline earth metal salts, or also ammonium salts or salts with organic amines.
  • salt formation can be caused by the addition of a strong organic solvent.
  • Particularly advantageous type A compounds are those in which the salt of the herbicide of the formula (I) is formed by replacing the hydrogen of the -SO 2 ⁇ NH group with a cation from the group of the alkali metals, alkaline earth metals and ammonium, preferably sodium.
  • the compounds of the formula I contain one or more asymmetric carbon atoms or else double bonds which are not indicated separately in the general formula, they nevertheless belong to the type A compounds.
  • the possible stereoisomers defined by their specific spatial form, such as enantiomers, diastereoisomers, Z and E isomers, are all encompassed by the formula I and can be obtained from mixtures of the stereoisomers by customary methods or else by stereoselective reactions in combination with the use of stereochemically pure ones Starting materials are produced.
  • the stereoisomers mentioned in pure form and also their mixtures can thus be used according to the invention.
  • compounds from group Aa) are of particular interest as combination partners of type A for the combinations of the invention, these being compounds of the general formula I in which R 1 (Ci-C ⁇ ) alkyl , (C 3 -C 4 ) alkenyl, (C 3 -C 4 ) alkynyl or (C 1 -C4) alkyl, the one to four times by radicals from the group halogen and (Ci-C 2 ) alkoxy is substituted, means R 2 is iodine, R 3 is methyl and Z is N.
  • phenylsulfonylureas of the general formula I bearing iodine substitution in the 4-position of the phenyl ring are in principle, for. B. from general formula 1 from ⁇ O 92/13845 and also their suitability as Synergistic partners for herbicides to be used in cereals or maize are already state of the art (cf. D3j, their outstanding suitability as combination partners for synergistic mixtures with other herbicides which are used in rice cannot be inferred from the state of the art.
  • R 2 represents iodine
  • R 3 is methyl and Z has the meaning N.
  • herbicidal compositions according to the invention contain a type A compound from group Aa) of the general formula I or its Salt in which R 1 is methyl, R 2 is iodine, R 3 is methyl and Z is N.
  • a special combination partner is the compound AI) 4-iodo-2- [3- (4-methoxy-6-methyl-l, 3,5-triazin-2-yl) ureidosulfonyl] benzoic acid methyl ester:
  • a possibly even more useful combination partner is the sodium salt of the compound AI), which is to be referred to as AI *).
  • one is preferably in the 5-position of the phenyl ring
  • Sulfonylureas of the general formula I bearing methylsulfonylamidomethyl substituents are used as compounds of the A) type.
  • the special sulfonylureas of group Ab) in combination with other herbicides of type B) are ideally suited to effectively control weed species that are difficult to control in rice crops. In particular, unexpected special effects against resistant harmful grass occur.
  • R 1 is methyl, ethyl, n- or isopropyl, n-, tert.-, 2-butyl or isobutyl, n-pentyl, isopentyl, n-hexyl, isohexyl, 1 , 3-dimethylbutyl, n-heptyl, 1-methylhexyl or 1, 4-dimethylpentyl means, R 2 is the meaning
  • R 3 is methoxy and Z is CH.
  • herbicidal compositions according to the invention comprise a type A compound from group Ab) of the general formula I or their salt, in which R 1 is methyl, R 2 CH 2 NHS0 2 CH 3 , R 3 OCH 3 and Z CH.
  • Compounds A2) belong to special combination partners:
  • the combination partners of type B are usually standard heroicides, but are selected under certain criteria. Without exception, they are herbicides which are selectively active in rice against undesirable plants.
  • the harmful plants to be controlled include, in particular, grasses and dicotyledons / cyperaceae.
  • the spelling “dicotyledons / cyperaceae” is intended to express that the effectiveness against dicotyledons and cyperaceae is given, but the effectiveness against dicotyledons is in the foreground.
  • Part of the type B herbicides is predominantly, or almost exclusively, active against grasses (subgroup Ba)), part is mainly against dicotyledons and cyperaceae (subgroup Bb)), another part is predominantly active against cyperaceae (subgroup Bc)) , while another group is effective against both Graser and dicotyledon / cyperaceae (subgroup Bd)).
  • the herbicidal composition of the invention is characterized in a particular embodiment in that it contains herbicides from the group Ba) which are herbicidally active amlides, in particular chloroacetanilides, thiocarbamates, as herbicides of the type B em or more selectively m rice against grasses , Chromium carboxylic acids, cyclohexanediones and cyclohexanedione oximes, tetrazoles, organophosphorus compounds, 2- (4-aryloxyphenoxy) propionic acids, preferably their esters, ureas, py ⁇ dmcarbothioates, butyramides, menthyl benzyl ethers and triazoles.
  • group Ba herbicidally active amlides, in particular chloroacetanilides, thiocarbamates, as herbicides of the type B em or more selectively m rice against grasses , Chromium carboxylic acids, cyclohex
  • the herbicidally active mixture of the invention is characterized in that it comprises herbicides of the type B em or more selectively active herbicides from the group which consists of
  • Pesticide Manual 10th ed. 1994, pp. 132-133;
  • R 1 halogen, (C ⁇ -C 4 ) alkoxy, (C ⁇ -C 4 ) alkyl, (C ⁇ -C 4 ) -
  • R 4 is hydrogen, (C1-C4) alkyl or -CO-O- (C1-C4) alkyl;
  • R ", R c , R 7 , R 8 R 9 independently of one another are hydrogen or (C 1 -C 4) alkyl or -CO-R 16 ;
  • R 11 is (C : -C 4 ) alkyl, (C1-C4) haloalkyl, phenyl, benzyl or -NR 17 R 18 ;
  • R i2 and R 13 independently of one another was serstof f or (Cr
  • R 16 is hydrogen, (C1-C4) alkyl, (C 1 -C 4 ) haloalkyl or (C 1 -C 4 ) alkoxy;
  • R 1 'and R 18 independently of one another are hydrogen or (C 1 -C 4 ) -alkyl; and n and m are independently 0, 1 or 2,
  • Pesticide Manual 11th ed. 1997, pp. 290-291;
  • Pesticide Manual 11th ed. 1997, p.1001-1003;
  • Pesticide Manual 10th ed. 1994, pp. 818-819;
  • Pesticide Manual 10th ed. 1994, pp.117-118;
  • the abovementioned compounds B1) to B8) are anilides, some of which belong to the subgroup of chloroacetanilides (compounds B1) to B4)) are.
  • the compounds B1) to B8) of subgroup Ba) are mainly active against harmful grasses.
  • the herbicides B1) to B8) mentioned are directed against grasses, for. B. annual grasses.
  • Butachlor also covers broad-leaved weeds in rice, as does butenachlor, which can also be used against aquatic weeds in rice; Thenylchlor fights in particular Echinochloa spp; while pretilachlor is effective against many seeds;
  • Mefenacet is particularly effective against Echinochloa crus galli; Naproaniiide, propanil and etobenzanide have the following main activity spectrum: broad-leaved and grassy weeds such as Amaranthus retroflexus, Digitaria spp.,
  • the compounds B9) to B12) are thiocarbamates, the action of which is best demonstrated in the
  • B13 is a representative of the quinoline carboxylic acids and is preferably used to control grass-like weeds (Echinochloa spp., Aeschynomene spp., Sesbania spp.) And other weeds in rice.
  • grass-like weeds Echinochloa spp., Aeschynomene spp., Sesbania spp.
  • B14) and Bl4a) are cyclohexanediones, which, surprisingly, also come within the scope of the combinations according to the invention Rice can be used against broad-leaf weeds and grasses.
  • B15) and B16) also belong to the group of cyclohexanediones in the broader sense.
  • it is cyclohexanedione oximes, which are preferably used to controlcht and perennial grasses in the
  • ⁇ ie .Tetrazoles also belong to group Ba) and are particularly effective against grasses in rice.
  • An important representative with the chemical structure mentioned is the compound B17).
  • Another interesting subgroup of subgroup Ba) are the organophosphorus compounds.
  • B18) is preferably used in the control of common grassers and seeders in rice.
  • B19) has a comparative spectrum of effects, namely: Annuelle Graser and Saaten n Reis.
  • the group Ba) also includes the family of herbicidally active 2- (4-aryloxyphenoxy) propionic acids.
  • An important representative is B20) with a preferred area of application against Graser Reis.
  • B21) is also usually used in the combinations of the invention to control individual and perennial grasses.
  • the joint use of B20) and / or B21) with a compound which is also effective as a safener, such as B22), can also have a particularly favorable effect in accordance with the invention.
  • Combinations with B22) according to the invention are of particularly great interest.
  • B22) acts as an acetyl-CoA carbolase inhibitor primarily against grassers and is due to the different metabolism of rice and weeds, especially well contracted in rice applications.
  • Group Ba also includes the family of the herbicidally active ureas.
  • An important representative of this chemical family is compound B23). This acts primarily against annual and perennial grasses.
  • menthyl benzyl ethers also belongs to group Ba).
  • An important element of this group is the compound B26). It works excellently against weeds in rice such as Echmochloa spp., Monocho ⁇ a vaginalis, Cyperus difformis;
  • T ⁇ azole as members of the subgroup Ba), together with compounds of the A type, have also been found to be very effective in suppressing undesired plant growth, especially of annual and perennial weeds in paddy rice, such as Ech ochloa oryzicola and Cyperus difformis.
  • herbicides belonging to the invention are those which contain type B herbicides from sub-group Bb).
  • one or more selectively used herbicides from the group which are active against dicotyls and partly also against cyperaceas are used, which include herbicides of the aryloxyalkyl carboxylic acid and dicamba type, nitrodiphenyl ether, azole and pyrazole, sulfonylurea, benzonitol, pyridmcaroonic acid and triazole.
  • herbicidal compositions which act as a type B em compound or more selectively in rice against dicotyledons and in some cases also cyperaceae
  • (4-Chloro-2-methylphenoxy) acetic acid predominantly used forms include MCPA-butotyl, MCPA-dimethylammonium, MCPA-isoctyl, MCPA-potassium, MCPA-Natriu, Pesticide Manual, 10th ed. 1994, p.638-640 ,
  • R is (C1-C4) alkyl
  • R c is hydrogen, halogen, cyano, (C1-C4) alkyl, (dC;) alkylthio or -NR R 12 , and R 8 are identical or different hydrogen or (C1-C4) alkyl, or and R 8 together with the nitrogen to which they are attached form a saturated 5 or 6-membered carbocyclic ring, is hydrogen or (C 1 -C 4 ) -alkyl, the latter optionally with one or several halogen atoms can be substituted, and R 11 u.
  • R 12 is the same or different hydrogen, (C ⁇ ⁇
  • R 1 "and R 12 together with the nitrogen to which they are attached can form a 3, 5 or 6-membered carbocyclic or aromatic ring in which a carbon atom is optionally separated by a 0-
  • Atom can be replaced; being particularly preferred
  • Combination partners .B28) to B33) of the type B compounds with selectivity in rice and activity against dicotyledons and in some cases against cyperaceae (subgroup Bb) with the herbicidal active ingredients B28) - B38) and their customary derivatives are suitable alone or in Combination of several extraordinarily good as
  • aryloxyalkyl carboxylic acids B28) to B31) are very well tolerated and they can provide excellent coverage of gaps in the weed spectrum to be controlled.
  • a third subgroup of compounds, the admixture of which to type A compounds to achieve herbicides Permitted for agents with excellent properties is subgroup Bc) the herbicide which is selective in rice and is active primarily against cyperaceae.
  • Type B substances with this activity profile are preferably found in the chemical substance classes of the ureas and benzofuranyl compounds or are in the form of the tri-clopyr or bentanzone.
  • a further advantageous embodiment of the invention is characterized in that it is a herbicide of type B B39) bentazone
  • All compounds B39) to B42) are herbicides which are selective in rice and which, with regard to the spectrum of the harmful plants to be controlled, correspond to the requirement profile described.
  • B41) is a benzofuranyl compound with a pronounced action against grasses and broad-leafed weeds in rice
  • B42) is a urea with a particularly pronounced action against cyperaceae and annual grasses in rice but also against dicotyledons.
  • Agents having a preferred action are obtained when the combination agent of the type Bc) B39) and / or B40) is contained in the agent according to the invention, and particularly nondesaturated harmful plants and also undesirable plants resistant to conventional agents can be controlled excellently.
  • a fourth subgroup of compounds whose admixture with compounds of type A enables herbicidal compositions with outstanding properties to be obtained is subgroup Bd), the herbicides which are selective in rice against grasses and dicotyledonous / cyperaceae.
  • Type B substances with this activity profile are preferably found in the chemical classes of 2, 6-dinitroanilines, pyrazoles, pyrimidinyloxobenzoic acids, oxadiazoles, anilides, diphenyl ethers, alkyl carboxylic acids, sulfonylureas, which are different from the sulfonylureas specified in formula I, 1 , 3, 5-triazines, pyridines and surprisingly also in the group of organophosphorus compounds.
  • the herbicidally active combinations contain, as type B herbicides, one or more herbicides which are selectively active in rice, predominantly against grasses and dicotyls / cyperaceae, from the group consisting of B43) pendimethalin
  • 2-dichloropropionic acid preferably also in its application form as sodium salt, namely as Dalapon sodium Pesticide Manual, 11th edition 1997, p.331-333;
  • group Bd consists. Of particular importance in group Bd) are, inter alia, the 2, 6-diminanoils such as pendimethalm (B43)) and clomazone (B44)).
  • Control of perennial lead leaf weeds in rice, combinations with B46) have proven particularly effective against grasses and seeds in rice such as Potamogeton distinctus, Sagitta ⁇ a trifolium, Alisma canaliculatum, etc. and combinations which, in addition to at least one type A compound, have the compound B47) , allow almost complete suppression of annealing and perennial weeds in rice, both on the cyperaceae side as well as on the dicotyledons or grassers.
  • Combinations with B48) are particularly useful for combating Ech ochloa spp. in "direct-seeded" rice, while the effectiveness of combinations which have B49) as a constituent is particularly noticeable, inter alia, against Echinochloa spp. paddy rice.
  • Combinations from group Bd) with oxadiazoles, anilides, diphenyl ethers or alkylcaroonic acids are also of particular interest.
  • Anilides such as the chloroacetanilides B52) or B53) and the sulfoanides, for example B54), should also be emphasized as combination partners for the type A compounds.
  • the anilides show a complementary effect on the side of the annual grasses and broad-leaved weeds, especially against Gallium aparme, Stellaria media, all types of Brassicaceae and Chenopodium spp., Amaranthus retroflexus, Solanum nigrum and Polygonum persicaria, in each case especially also in the post-emergence process.
  • Diphenyl ethers or alkyl carboxylic acids are also interesting partners for type A sulfonylureas.
  • Diphenyl ether B55 helps to close the efficacy gaps that may be present on the grass and broad-leafed weed side.
  • B56) has a reinforcing effect, especially when combating halophytic and semi-aquatic grass weeds.
  • the herbicidally active combinations contain as
  • R 2 halogen, N0 2 , CF 3 , CN, (dC) -alkyl, (dC 4 ) - alkoxy, (C ⁇ -C 4 ) -alkylthio or ((C ⁇ -C 4 ) -alkoxy) - carbonyl and n 0, 1, 2 or 3 or b) R 1 optionally unsaturated (-C-C 8 ) alkoxy which is substituted by halogen, optionally unsaturated (Ci-C ⁇ ) alkoxy, a radical of the formula ((C: -C 6 ) -Alkyl) -S-, ((dC 6 ) -alkyl) -SO-, ((-C ⁇ -C 6 ) - alkyl) -S0 2 -, ((-C ⁇ -C 6 ) -alkyl) -O-CO-, N0 2 , CN or phenyl; furthermore (C 2 -C 8 ) -al
  • R (C 2 -C 8 ) alkenyl or alkynyl, phenyl, phenoxy, where the radicals mentioned for R 2 are unsubstituted or are substituted by halogen, (C1-C4) -alkoxy or (C 1 -C 4 ) -alkylthio, or (C 1 -C 4 ) -alkylsulfonyl or - sulfinyl and n 1, 2 or 3 or d) R 1 in each case 2-position on the phenyl radical halogen, methoxy, ethyl or propyl,
  • R 3 is hydrogen, saturated or unsaturated
  • Residues unsubstituted or substituted by halogen, (-C ⁇ C) alkoxy or (C 1 -C 4 ) alkylthio, Y 0 or S and E are CH or N
  • the sulfonylureas of the general formula IV inter alia, from DE-A- 38 16 704.2 (EP-A-0 342 569), DE-A-38 16 703.4 (EP-A-0 342 568) and DE-A-39 09 053.1 (EP-A-0 388 771) are known, and in which
  • Compounds B57) to B65) are certain sulfonylureas, the selection and suitability of which is critical for combinations according to the invention. They are structurally different from the sulfonylureas of the general formula I. Together with Type A partners, they all result in excellent combinations with high selectivity in rice and effectiveness against grasses,
  • Cyperaceae and dicotyledonous harmful plants It is often the case that the focus of the combinations according to the invention can be achieved by suitable choice of the type B connection to influence the controlled spectrum of harmful plants.
  • sulfonylureas B57) or B58 result in combinations with high selectivity against annual and perennial weeds in rice, such as: Butomus umbellatus, Scirpus ma ⁇ timus, Scirpus mucronatus, Alisma plantago-aquatica, Alisma lanceolatum, Sparganium erectum, Typera spp.
  • the heat spectrum of combinations with sulfonylurea B59 mainly comprises the selective control of annual and perennial broad-leaved weeds, seeds and grasses (barnyard grass) in rice, while B60) focuses primarily on Alisma, annual Cyperus, Elocharia, Marsilea, Potamogeton and Sagitta ⁇ a spp. , Monocho ⁇ a vaginalis and Sphenoclea zeylanica are effective.
  • Combinations according to the invention with sulfonylurea B61 have proven to be highly selective against annual and perennial leaflet weeds and seeds in rice, while B62) selectively against Cyperus serotmus, Eleocharis kuroguwai, Sagittaria pygmaea and similar m
  • PhenoxyS._fonylureas B63 can close gaps in effectiveness in the area of mono- and dicotyledon weeds in rice, similar to mixtures with B64) and / or B65).
  • herbicidal agents which are selective in rice against dicotyledons, cyperaceae and grasses, sulfonylureas for which biological data are given in the example.
  • group Bd are also 1, 3, 5-tr ⁇ azme, pyridme, organophosphorus compounds and others individual representatives of certain chemical substance class of increased importance when used in combinations according to the invention.
  • the herbicidally active combinations comprise herbicides of the type B em or more selectively active herbicides from the group consisting of, against grasses and dicotyledons and cyperaceae
  • the compounds B1) to B73) are, for example, herbicides which are known from the "source given for the particular compound and are used specifically in combination with the A compounds of the invention, m rice and m transgenic rice.
  • the formula is regularly provided for clarification with reference to modifications of the basic substances used in public.
  • all commonly used modifications of the B compounds belong to the present invention, even if they are not expressly mentioned individually -B-dressings are common, these also belong to the invention, in some cases reference has also been made to these forms (for example fenoxaprop-ethyl and fenoxaprop-P ⁇ ethyl etc.).
  • Combinations of the active ingredients A + B show superadditive effects, ah with the same control of the harmful plants, the herbicidal compositions according to the invention make it possible to reduce the application rate and / or the m to increase rice cultures. Both make sense both ocnom ⁇ scn and ecologically.
  • the choice of the quantities to be used by components A + B, the ratio of components A: B and the time series fc-.de of the application are as well for example, the wording to be chosen depends on a number of factors.
  • herbicidal compositions according to the invention are characterized in that they have a synergistically active content of a combination of the compounds of the formula I or their salts (type A compounds) with compounds from group B. It should be emphasized that even in combinations with
  • the extremely low application rate of the sulfonylureas of the general formula I from subgroup Aa) is particularly surprising.
  • the application rate for example the compound AI) or AI *
  • AI is again drastically reduced compared to the application rate as is known for the use of AI) or AI *) for combating harmful plants in cereals or maize.
  • the application rates of compounds of type B are usually:
  • A: B of the combined herbicides, as mentioned, and their application rates can vary within wide limits.
  • a range according to the invention in terms of quantity (wt / wt) comprises approximately A: B such as 1: 20,000 to approximately 200: 1.
  • Agents with application rate ratios A: B which are between 1: 4000 and 50: 1 are particularly useful.
  • the following picture emerges for the various subgroups, ie the following
  • Weight ratios are preferably used:
  • At least one herbicidal active ingredient from the group of substituted phenylsulfonylureas of the general formula I and their agriculturally accepted, i.e. acceptable and contractual, salts
  • R 2 is I or CH 2 NHS0 2 CH 3 ; R represents methyl or methoxy; and Combination with at least one herbicidally active compound from the group of the compounds B ', which consists of B1) butachlor, B2) butenachlor, B3) thenyl chlorine, B4) pretilachlor, B5) mefenacet, B5a) Bay FOE 5043, B6) naproanilide, B7) propanil,
  • B63a ethoxysulfuron (HOE 095404), B64) Az ⁇ msulfuron (DPX-A8947), B65) Nicosulfuron, B66) Prometryn, B67) Simetryn, B68) Thiazopyr, B69) Pyrazophos, B70) Pentoxazone, B71) Indanofan, B72) LGC 40863 and B73) MY 100 If B ' ' at least one of the compounds from group B '' must also belong to group B '.
  • the active ingredient combinations according to the invention can be present both as mixed formulations of the two components, which are then used in a customary manner diluted with water, or else as so-called tank mixes by diluting the separately formulated components with water.
  • the active ingredients of types A and B can be formulated in different ways, depending on which biological and / or chemical-physical parameters are specified.
  • WP Wettable powder
  • EC emulsifiable concentrates
  • SP water-soluble powders
  • SL concentrated emulsions
  • EW concentrated emulsions
  • SC capsule suspensions
  • CS dispersions based on 01 or water
  • SC suspoemulsions
  • suspension concentrates dusting agents ( DP), miscible solutions (OL), pickling agents
  • WP water-soluble wettable powders
  • WG water-dispersible granules
  • EC water-emulsifiable granules
  • SE suspoemulsions
  • SC oil suspension concentrates
  • the herbicide combinations of the invention are produced particularly advantageously by combining the compounds of the formula I or their salts (type A compounds) with one or more compounds of the type B analogously to a conventional crop protection formulation from the group comprising water-soluble wettable powders (WP), water-dispersible granules (WDG), water-emulsifiable granules (WEG),
  • WP water-soluble wettable powders
  • WDG water-dispersible granules
  • WEG water-emulsifiable granules
  • SE Suspoemulsions
  • SC oil suspension concentrates
  • Spray powders are preparations which are uniformly dispersible in water and, in addition to the active ingredients, in addition to a diluent or inert substance, are also surfactants of an ionic and / or nonionic type (wetting agents, dispersants), for. B.
  • polyoxyethylated alkylphenols polyoxyethylated fatty alcohols and fatty amines, fatty alcohol polyglycol ether sulfates, alkane sulfonates or alkylarylsulfonates, sodium lignosulfonate, 2,2'-dinaphthyimethane-6, 6'-disulfonic acid sodium, sodium dibutylnaphthalenesulfonate or sodium oleylmate.
  • Emulsifiable concentrates are obtained by dissolving the active ingredient or ingredients in an organic solvent, e.g. B. butanol, cyclohexanone, dimethylformamide, xylene or higher-boiling aromatics or hydrocarbons with the addition of one or more surfactants of ionic and / or nonionic type (emulsifiers).
  • organic solvent e.g. B. butanol, cyclohexanone, dimethylformamide, xylene or higher-boiling aromatics or hydrocarbons
  • surfactants of ionic and / or nonionic type (emulsifiers) e.g. B. butanol, cyclohexanone, dimethylformamide, xylene or higher-boiling aromatics or hydrocarbons.
  • alkylarylsulfonic acid calcium salts such as calcium dodecylbenzenesulfonate or nonionic emulsifiers
  • fatty acid polyglycol esters alkylaryipolyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensation products (e.g. Block copolymers), alkyl polyethers, sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters or other polyoxyethylene sorbitan esters.
  • Dusting agents are obtained by grinding the active ingredient or ingredients with remotely distributed substances, e.g. B. talc, natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.
  • remotely distributed substances e.g. B. talc, natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.
  • Granules can either be produced by spraying the active ingredient or the active ingredients onto adsorbable, granulated inert material or by applying active ingredient concentrates by means of adhesives, e.g. As polyvinyl alcohol, polyacrylic acid sodium or mineral oils, on the surface of carriers such as sand, kaolmite or granulated inert material.
  • adhesives e.g. As polyvinyl alcohol, polyacrylic acid sodium or mineral oils, on the surface of carriers such as sand, kaolmite or granulated inert material.
  • Water-dispersible granules are generally milled using customary processes such as spray drying,
  • Suitable active ingredients can also be granulated in the manner customary for the production of fertilizer granules - if desired in a mixture with fertilizers.
  • the agrochemical preparations according to the invention generally contain 0.1 to 99% by weight, in particular 2 to 95% by weight, very particularly preferably 3 to 92% by weight, of active ingredients of types A and B, in addition to conventional formulation auxiliaries.
  • the concentrations of the active ingredients A + B can vary in the formulations.
  • the active ingredient concentration is e.g. B. about 10 to 95 wt .-%, the rest of 100 wt .-% consists of conventional
  • Formulation ingredients In the case of emulsifiable concentrates, the active substance concentration can be about 1 to 85% by weight, preferably 5 to 80% by weight. Dusty Formulations contain about 1 to 25% by weight, mostly 5 to 20% by weight of active ingredients, sprayable solutions about 0.2 to 25% by weight, preferably 2 to 20% by weight of active ingredients.
  • the active ingredient content depends in part on whether the active compound is liquid or solid and which granulation auxiliaries and fillers are used. As a rule, the content of the water-dispersible granules is between 10 and 90% by weight.
  • the active ingredient formulations mentioned may contain the customary adhesives, wetting agents, dispersants, emulsifiers, penetrants, preservatives, antifreeze agents and solvents, fillers, dyes and carriers, defoamers, evaporation inhibitors and the pH and Agents influencing viscosity.
  • the combinations according to the invention achieve a reduction in the absolute application rate compared to the single application of a herbicidal active ingredient.
  • it is advantageous to use these together in a mixture or in succession in succession together with safeners or anti ⁇ ots. Suitable safeners or antidots for the combinations according to the invention are, for. B.
  • EP-A-333 131 ZA-89/1960
  • EP-A-269 806 US-A-4, 891,057
  • EP-A-346 620 AU-A-89/34951
  • PCT / EP 90/01966 WO-91/08202
  • PCT / EP 90/02020 WO-91/078474
  • Other suitable safeners are known from EP-A-94 349 (US-A- 4,902,304), EP-A-191 736 (US-A-4, 881, 966) and EP-A-0 492 366 and the literature cited therein.
  • the herbicidal mixtures or application combinations of the invention are characterized by an additional content of
  • X is hydrogen, halogen, (-CC 4 ) -alkyl, (C1-C4) -alkoxy, nitro or (C 1 -C 4 ) -haloalkyl,
  • Alkanediyl chain which can also be substituted with one or two (C1-C4) -alkyl radicals or with [(C 1 -C 3 ) -alkoxy] carbonyl, preferably -CH 2 -,
  • R 1 is hydrogen, (dC 18 ) alkyl, (C 3 -C 12 ) -
  • Alkynyl where the above C-containing radicals are unsubstituted or one or more times, preferably up to three times, by identical or different radicals from the group comprising halogen, hydroxy, (-CC 8 ) alkoxy, (-CC 8 ) - Alkylthio, (C 2 -C 8 ) alkenylthio, (C 2 - C 8 ) alkynylthio, (C 2 -C 8 ) alkenyloxy, (C 2 -C 8 ) -
  • R 2 is hydrogen, (-CC 8 ) alkyl, (dC 8 ) -
  • Haloalkyl, (C3-C12) -cycloalkyl or optionally substituted phenyl and R 3 is hydrogen, (-C-C 8 ) -alkyl, (C ⁇ -C 8 ) - haloalkyl, (C1-C4) -alkoxy- (C1-C4) - alkyl, (-C-C 6 ) hydroxyalkyl, (C3-C12) - cycloalkyl or tri- ((C1-C4) alkyl) - are silyl, or the salts of the compounds mentioned.
  • Alkyl means, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, i-butyl, t-butyl and 2-butyl, pentyls, in particular n-pentyl and neo-pentyl, hexyls, such as n-hexyl and i- Hexyl and 1,3-dimethylbutyl, heptyls such as n-heptyl, 1-methylhexyl and 1,4-dimethylpentyl;
  • Alkenyl means, for example, allyl, l-methylprop-2-en-l-yl, but-2-en-l-yl, but-3-en-l-yl, l-methyl-but-3-ene and 1 -
  • Alkynyl means, inter alia, propargyl, but-2-yn-l-yl, but-3-yn-l-yl, l-methyl-but-3-yn;
  • Cycloalkyl preferably has 3 to 8 carbon atoms and is, for. B. for cyclobutyl, cyclopentyl, cyclohexyl or cycloheptyl. Cycloalkyl can optionally carry up to two (C 1 -C 4) alkyl radicals as substituents.
  • Halogen means fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, in particular fluorine or chlorine;
  • Haloalkoxy is for example 0CF 3 , OCHF 2 , OCH 2 F, CF 3 CF 2 0, CF 3 CH 2 0;
  • Aryl preferably has 6 to 12 carbon atoms and is e.g. B. phenyl, naphthyl or biphenyl, preferably phenyl. The same applies to residues derived therefrom, such as aryloxy, aroyl or aroylalkyl;
  • optionally substituted phenyl is, for example, phenyl which is unsubstituted or one or more, preferably one, two or three times, by identical or different radicals from the group halogen, (C 1 -C 4) -alkyl, (C 1 -C 4 ) alkoxy, (C1-C4) haloalkyl, (C1-C4) haloalkoxy, (C 1 -C4) alkylthio, (C2-C5) alkoxycarbonyl, (C 2 -C 5 ) alkylcarconyloxy, carbonamide, (C 2 -C 5 ) alkylcarbonylammo, D ⁇ [(C ⁇ -C.
  • Alkyl] ammocarbonyl and nitro is substituted, for example o-, m- and p-tolyl, dimethylphenyls, 2-, 3- and 4-Cn_orphenyl, 2-, 3- and 4-t ⁇ fluor- and -
  • R 1 is hydrogen, (-CC 8 ) alkyl, (C 3 -C 7 ) -
  • R 2 is hydrogen, (C 1 -C 8 ) alkyl, (C 1 -C 6 ) haloalkyl, (C 3 -C 7) cycloalkyl or phenyl and R 3 is hydrogen, (C 1 -C 8 ) alkyl, (dC 8 ) -Haloalkyl,
  • compositions according to the invention are also of particular interest, wherein in the compounds of the formulas Cl and C2,
  • X is hydrogen, halogen, methyl, ethyl, methoxy, ethoxy, (C ⁇ -C 2 ) -haloalkyl, preferably hydrogen, halogen or (C1-C2) -
  • Haloalkyl means.
  • compositions according to the invention are preferred, the compounds of the formula C1
  • X is hydrogen, halogen, nitro or (C 1 -C4) -
  • R 2 is hydrogen, (C ⁇ -C 8 ) alkyl, (C ⁇ -C 6 ) haloalkyl, (C 3 -C7) cycloalkyl or phenyl and
  • R 3 is hydrogen, (C ⁇ -C 8 ) alkyl, (C -C 8 ) haloalkyl, ((C1-C4) alkoxy) - (C1-C4) alkyl, (C ⁇ -C 6 ) - hydroxyalkyl, ( C 3 -C 7 ) cycloalkyl or tri-
  • compositions according to the invention are also preferred, wherein in the compounds of the formula C2,
  • X is hydrogen, halogen or (C ⁇ -C) -
  • Z is a radical of the formula OR 1 , R 1 is hydrogen, (C ⁇ -C 8 ) -alkyl, (C ⁇ -C 4 ) -haloalkyl,
  • R 2 is hydrogen, (C ⁇ -C 8 ) alkyl, (C ⁇ -C 4 ) haloalkyl or (C 3 -C7) cycloalkyl, preferably
  • R 3 is hydrogen, (C ⁇ -C 8 ) alkyl, (C -C 4 ) haloalkyl, (dC 4 ) hydroxyalkyl, (C 3 -C7) cycloalkyl, ((C1-C4) alkoxy) - (C1 -C4) alkyl or tri- ((C x - C 2 ) alkyl) silyl, preferably H or (C 1 -C4) -
  • compositions according to the invention with compounds of the formula Cl, in which W W3
  • R 1 is hydrogen, (C ⁇ -C 8 ) alkyl, (C ⁇ -C 4 ) haloalkyl, (dC 4 ) hydroxyalkyl, (C 3 -C 7 ) cycloalkyl, ((d ⁇ C 4 ) alkoxy) - (-CC 4 ) alkyl, tri- ((C ⁇ -C 2 ) alkyl) silyl, preferably (C ⁇ -C 4 ) alkyl, and R 2 (C ⁇ -C 8 ) alkyl or (dd) - Haloalkyl, preferably C ⁇ -haloalkyl.
  • R 1 is hydrogen, (C ⁇ -C 4 ) alkyl or ((C ⁇ -C 4 ) -
  • Alkoxy) -carbonyl- (dd) -alkyl preferably ((dC 4 ) -alkoxy) -CO-CH2-, ((C1-C4) -alkoxy) -CO- C (CH 3 ) H-, HO-CO- CH 2 - or HO-CO-C (CH 3 ) H-, mean.
  • the compounds of the formulas C1 are from EP-A-0 333 131, EP-A-0 269 806, EP-A-0 346 620, international patent application PCT / EP 90/01966 and international patent application PCT / EP 90/02020 and there known literature cited or can be prepared by or analogously to the methods described therein.
  • the compounds of the formula C2 are known from EP-A-0 086 750, EP-A-0 094 349 and EP-A-0 191 736 and the literature cited therein, or can be based on or analogous to those described there Process are made. They are also proposed in DE-A-40 41 121.4.
  • antidots or safeners or groups of compounds which have proven to be safe or antidots for the above-described product combinations of the invention include:
  • R * CH 2
  • compounds such as (5-chloro-8-chmolmoxy) acetic acid- (1-methyl-hex-l-yl) ester (C2-1), (5-chloro-8-chmolmoxy) -acetic acid- (1,3-dimethyl-but-l-yl) ester (C2-2), (5-chloro-8-chomoloxy) -acetic acid-4-allyl-oxy-butyl ester (C2-3),
  • active substances of the type of phenoxyacetic or - propionsaurede ⁇ vate or aromatic carboxylic acids such as. B. 2.4-
  • the herbicidal compositions of the invention are characterized by an additional content of
  • R 1 carboxv, formyl or another acyl radical or a derivative of the latter 3 groups
  • R 2 is hydrogen, halogen, -CC 18 alkyl, C 3 -C 8 cycloalkyl, C 2 -C 8 aikenly, C 2 -C 8 alkynyl, C ⁇ -C 18 alkenyloxy, C 2 -C 8 - Aik ⁇ nyloxy, C ⁇ -C 18 alkylthio, C 2 -C 8 alkenylthio, each of the latter 9 radicals unsubstituted or by one or more radicals from the group halogen, nitro, cyano, C ⁇ -C 4 alkoxy or (C ⁇ - C 8 - alkoxy "carbonyl substituted 1, or (C ⁇ -C 8 - alkoxy, carbonyl,
  • R 3 and R "" independently of one another are an aliphatic, araliphatic or heteroaraliphatic radical having 1 to 30 C atoms which are unsubstituted or substituted by one or more functional groups, or an aromatic or heteroaromatic radical which is unsubstituted or substituted,
  • agents of particular interest are those which, in addition to A and B compound (s), have a type C3 compound, wherein in the general formula C3
  • R 1 is a radical of the formula
  • R, R ⁇ 'R 5 , R 6 , R 7 , Y, T, Z, Q, A lr X and q are as defined below,
  • R is hydrogen or an aliphatic, aromatic, heteroaromatic, araliphatic or heteroaraliphatic radical having 1 to 30 carbon atoms, which is unsubstituted or substituted by one or more functional groups,
  • R a , R b and R c are independently C ⁇ -C-alkyl, C 2 -C-alkenyl, dd-alkynyl, phenyl or substituted phenly,
  • Y, Z independently of one another are oxygen, sulfur in its various oxidation states, or -NR e , where R e is defined analogously to R 5 or R 6 ,
  • R 5 , R 6 are the same or different and are independently hydrogen, Ci-d-alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, (C ⁇ -C 4 alkyl) carbonyl, each of which 4 latter residue unsubstituted or by one or more substituents from the group containing halogen, C ⁇ -C 8 haloalkoxy, nitro, cyano, hydroxy, C ⁇ -C 8 alkoxy and a C ⁇ -Cc alkoxy group, in which one or more CH 2 ⁇ Groups are replaced by oxygen, and CC 8 alkylthio, C ⁇ -C 6 - alkylsulfonyl, C 2 -C 8 alkenylthio, C 2 -C 8 alkynylthio, C 2 -C 8 alkenyloxy, C 2 -C 8 alkynyloxy , C 3 -C 7 cycloalkyl, C 3 -C 7 -
  • R, R b and R c independently of one another are C ⁇ -C 4 -alkyl, C 2 - d-alkenyl, C 2 -C 4 -alkynyl or unsubstituted or substituted phenyl, or C 3 -C 8 cycloalkyl, C 3 -C 8 cycloalkenyl, heterocyclyl with 3 to 7 ring atoms, aryl, heteroarly or arylcarbonyl,
  • R 5 , R 6 together form a C-C4-alkylene chain or C 2 -d-
  • Alkenylene chain which is unsubstituted or substituted by 1 or 2 radicals from the group methyl, ethyl, methoxy, ethoxy and halogen, and
  • R 7 is hydrogen, dd-alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, unsubstituted or substituted dC 12 aryl or heteroaryl, benzyl, C ⁇ -C 4 alkoxy, acyloxy, hydroxy, - NH- CO-NH 2 , -NH-CS-NH 2 , mono- and di- (C ⁇ -C 4 -alkyl) -amino, acyiamino, (C ⁇ -C 4 -alkyl) -sulfonylamino,, d-C ⁇ 2 -aryloxy, Heteroaryloxy, arylsulfonylamino or arylamino, in which aryl or heteroaryl is unsubstituted in the latter 4 radicals or by one or more radicals from the group halogen, nitro, (C ⁇ -C 4 ) alkyl, (C ⁇ -C 4 ) alkoxy,
  • 1 is a serial number which, if q is not equal to 0, all all
  • Xi independently 0, S, NR 9 , N- (A 1 X 1 ) q -R
  • Ai independently of one another unsubstituted or substituted dd-alkylene, C 2 -d-alkenylene, C 2 -C 6 -alkyl, dd-cycloalkenylene, heterocyclylene, arylene or heteroarylene and
  • R, R independently of one another are H, C ⁇ -C 4 alkyl, C 2 -C 4 alkenyl, dd-alkmyl, C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkenyl, heterocyclyl, aryl or heteroaryl.
  • agents according to the invention which are of the highest interest are those which have one or more compounds of the type C3, where in the general formula C3 at least one of the radicals R 3 and R 4 independently of one another is a radical of the formula
  • (U) f_.r are the same or different radicals which are independently hydrogen, cyano, nitro, amino or C -C 8 -haloalkyl, -C-C 8 -haloalkoxy, C -C 8 -alkyl, C x - d-al ⁇ oxy , Mono- (C ⁇ -C 4 -alkyl) -ammo, di- (C ⁇ -C 4 -alkyl) - amino, C ⁇ -C 8 -Alkylth ⁇ o or dC 8 -alkylsulfonyl, each of the latter 8 residues unsubstituted or by one or more identical or different substituents from the group containing halogen, C ⁇ -C 8 haloalkoxy, nitro, cyano, hydroxy, C ⁇ -C 8 alkoxy and a C ⁇ -C 8 alkoxy group, wherein one or more CH 2 groups are replaced by oxygen, C ⁇ -C 8 -Alkylth ⁇ o, C
  • o is an integer from 1 to 5 and
  • p is an integer from 1 to 7
  • a monocyclic or bicyclic heteroaryl radical from the group consisting of furyl, thienyl, pyrrolyl, pyrazolyl, thiazolyl, oxazolyl, pyridmyl, pyrimidmyl, pyrazmyl,
  • each of the latter 7 radicals independently of one another or unsubstituted by one or more radicals from the group containing halogen, cyano, Tmo, nitro, hydroxy, C ⁇ -C 8 alkyl, the latter only in the case of cyclic radicals, C ⁇ -C 8 haloalkyl , C ⁇ -C 8 - Al ⁇ oxy, C 2 -C 8 -alkenyloxy, C 2 -C 8 -alkyloxy, C ⁇ -C 8 - haloalkoxy, C 2 -C 8 -alkenylthio, C 2 -C 8 -alkylthio, C 3 - C-- dc oalkyl, C 3 -C 7 cycloalkoxy, residues of the formulas - NR * R ** and -CO-NR * R ** and -0-CO-NR * R ** where R * and R ** _- the latter radicals independently of one another
  • C ⁇ -C 8 alkyl C 2 -C 8 alkenyl, C 2 -C 8 alkyl, benzyl, phenyl or substituted phenyl or together with the N atom a 3- to 8-gl ⁇ edr ⁇ gen Heterocylcus, which also contain up to 2 further heteroatoms from the group N, 0 and S and can be substituted by C ⁇ -C-alkyl, mean, as well as (C ⁇ -C 8 -alkoxy) carbonyl, (CC 8 -akoxy) - thiocarbonyl, (C 2 -C 8 alkenyl) carbonyl, (C ⁇ -C 8 alkoxy) thiocarbonyl, (C 2 -C 8 -
  • R "0- CHR"'CH (OR) -CC 6 -alkoxy where the R "independently of one another are CC 4 -alkyl or together are a C - - alkylene group and R""is hydrogen or C ⁇ -C - Is alkyl, is substituted.
  • Agents containing a compound C3 are also important and interesting, wherein in the general formula C3 R 2 is hydrogen, dC 4 -alkyl, C ⁇ -C 4 -alkoxy or C 5 -C 6 -cycloalky_ and at least one of the radicals R 3 , R 4 is a radical of the formula
  • (U) stand for identical or different radicals which independently of one another are hydrogen, halogen, such as fluorine, chlorine, bromine and iodine, cyano, nitro, amino, C ⁇ -d-alkoxy, mono- (C ⁇ -d-alkyl) -amino, Di- (-CC 4 -alkyl) -ammo, C1-C4-alkylthio or C ⁇ -C 4 alkylsulfonyl mean and
  • o is an integer from 1 to 3 and
  • p is an integer from 1 to 3, or one of the radicals
  • R 3 , R independently of one another are a monocyclic or bicyclic heteroaryl radical from the group consisting of furyl, thienyl, pyrrolyl, pyrazolyl, thiazoyl, oxazolyl, pyridmyl, pyrimidmyl, pyrazmyl, py ⁇ dazmyl and chmolmyl, which is unsubstituted or substituted by one or three of the abovementioned radicals , mean
  • agents which have one or more C3-like compounds of the general formula C3, in which R ", R 4 independently of one another are identical or different radicals of the formula
  • R is hydrogen, -CC 8 -alkyl, dd-cycloalkyl, C 2 -C 8 -alkynyl, heterocyclyl, phenyl or heteroaryl,
  • each of the latter 7 radicals independently of one another unsubstituted or by one or more radicals from the group containing halogen, cyano, thio, nitro, hydroxy, C,-C-alkyl, the latter only in the case of cyclic radicals, C ⁇ -C 4 -haloalkyl, C ⁇ -C-alkoxy, C2-C4-alkenyloxy, C 2 -C 4 -alkynyloxy, C ⁇ -d-haloalkoxy, C 1 -C4-alkylthic, C 2 -C4-alkenylthio, C 2 -C 4 -alkynylthio, C 5 -C 6 - cycloalkyl, C 5 -C 6 cycloalkoxy, amino, mono- and di- (CC 4 - alkyl) -arr.mo, (C ⁇ -d-alkoxy) -carbonyl, residues of the formulas - SiR ' 3 ,
  • R ⁇ a radical of the formula -CO-R, --NNIRR fr RR9 g or means.
  • R, R together form a C 2 -C 4 alkylene chain or dd-alkenyl chain which is unsubstituted or substituted by 1 or 2 radicals from the group consisting of methyl, ethyl, methoxy, ethoxy and halogen, and
  • the safeners (antidotes) from groups a) to j) above (in particular compounds of the formulas Cl, C2 and C3) reduce or prevent phytotoxic effects which can occur when the product combinations according to the invention are used in crops without the effectiveness of the herbicides against harmful plants to affect.
  • the field of use of the mixtures of herbicides according to the invention can be expanded very considerably and, in particular, the use of safeners enables the use of combinations which have hitherto been limited or unsuccessful, ie combinations which do not contain safeners in low doses with little broad effect led to insufficient control of the harmful plants.
  • the herbicidal mixtures according to the invention and the safeners mentioned can be applied together (as a finished formulation or in a tank mix process) or in succession in any order.
  • the weight ratio of safener: herbicide (group A, ie compounds of the formula I) can vary within wide limits and is preferably in the range from 1: 100 to 100: 1, in particular from 1: 100 to 50: 1.
  • the optimum amounts of herbicides in each case (Type A and Type B compounds) and safeners are usually dependent on the type of herbicide mixture used and / or on the safener used and on the type of crop to be treated.
  • the safeners of type C can be used for the pretreatment of the seed of the crop (dressing the seeds) or the seed furrows can be introduced before sowing or used together with the herbicide mixture before or after emergence of the plants.
  • Pre-emergence treatment includes both the treatment of the cultivated area before sowing and the treatment of the sown but not yet overgrown cultivated areas.
  • Co-application with the herbicide mixture is preferred.
  • Tank mixes or ready formulations can be used for this.
  • the required application rates of the safeners can vary within wide limits, depending on the indication and the herbicide used, and are generally in the range from 0.001 to 1 kg, preferably 0.005 to 0.2 kg, of active compound per hectare.
  • a particularly favorable combination can be seen in the joint use of AI or AI *) and C3-1, at least with a type B connection.
  • the safener C3) in particular C3-1, is particularly advantageous in two ways. Both by protecting the rice crops from undesirable damage by the type A herbicides and by synergistically enhancing the action of the individual herbicides from group A.
  • herbicidal compositions which contain type A compounds in an amount of 0.5 to 60 g ai / na in combination with the safener C3) m in an amount of 10 to 200 g ai / ha. Also favorable are herbicidal compositions which are distinguished by a weight ratio of type A compounds: C3) in the range from 1:40 C to 20: 1, preferably 1: 200 to 10: 1.
  • a particular embodiment of the invention also relates to herbicidal compositions which have a type A compound, preferably the compound AI) or AI *) in an amount of 0.1 to 10 g ai / ha in combination with C3) in an amount of 10 De-air 100 g ai / ha.
  • the formulations present in the commercially available form are optionally diluted in the customary manner, for example in the case of wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules, using water. Dust-like preparations, ground or * . Scatter granules and sprayable solutions are usually no longer diluted with other inert substances before use.
  • the invention also relates to a method for controlling unwanted plants, which is characterized in that a nerpicidally effective amount of a combination of active ingredients A + B according to the invention is applied to this or the cultivated area.
  • the active ingredients can be applied to the plants, parts of plants, plant seeds or the area under cultivation.
  • the compounds of the formula (I) or their salts (type A compounds) are applied in amounts of from 0.1 to 100 g ai / ha, preferably from 0.5 to 6C g ai / ha, very particularly preferably between 2 and 4C g ai / na, applied, while the application rates for the compounds of type B are from 1 to 5000 g ai / ha. It is preferred to apply the active compounds of types A and B at the same time or at different times in a weight ratio of 1: 20000 to 200: 1. Still special Preferred is the joint application of the active ingredients in the form of tank mixtures, the optimally formulated concentrated formulations of the individual active ingredients being mixed together with water in the tank and the spray mixture obtained being applied.
  • Modification of the process uses herbicidal compositions with the active compound combinations according to the invention for the selective control of undesired plants.
  • the process for the selective control of harmful plants is particularly favorable when the combination partners of type B) from subgroups Ba) to Bd) are used if the herbicidal compositions of the invention are used in rice.
  • the communication partners B28) to B33) from group Bb) mostly belong to the growth herbicides, which have the effect of the type compounds in rice especially in the control of weeds from the spectrum of dicotyls but also significantly improve and improve against cyperaceae.
  • the compounds from subgroup Bc) are widespread active ingredients that can be used to increase the effectiveness of type A compounds in combating primarily cyperaceae, especially in rice.
  • the azoles and pyrazoles from subgroup Bd) can be used particularly advantageously with comparatively low application rates to control dicotyledon weeds in rice. However, they also work particularly well against a wide range of harmful grasses, just as they control cyperaceae.
  • the herbicidal combinations according to the invention can advantageously also be used in transgenic rice crops to control unwanted plants.
  • Transgenic cultures are those in which the plants are made resistant to HerDicides or pesticides through genetic manipulation. Rice crops modified in this way then allow selective use.
  • At least one herbicidal active ingredient from the group of substituted phenylsulfonylureas of the general formula I and their agriculturally accepted, ie acceptable and compatible, salts
  • R 1 (dC 8 ) -alkyl, (C 3 -C 4 ) -alkenyl, (C 3 -C 4 ) -alkynyl or (C ⁇ -C 4 ) -alkyl, which is one to four times by radicals from the group halogen and / or (C ⁇ -C 2 ) alkoxy is substituted;
  • R 2 is I or CH 2 NHS0 2 CH 3 ;
  • R J represents methyl or methoxy; and ZN or CH;
  • Bl Butachlor, B2) Butenachlor, B3) Thenylchlor, B4) Pretilachlor, B5) Mefenacet, B5a) Bay Foe 5043, B6) Naproanilid, B7) Propanil, B8) Etobenzanid, B9) Dimepiperate, BIO) Molinate, Bll) Thiobencarb, B12) pyributicarb, B13) quinclorac, B14a) sulcotrione,
  • Bd active in rice, mainly against grasses and otyls and cyperaceae harmful plants, ⁇ rbicides selected from the group consisting of 3) pendimethalin, B44) clomazone, B45) benzofenap,; ⁇ ) pyrazolynates, B47) pyrazoxyfen, B48) KIH 2023,; 9) KIH 6127, B50) oxadiazon, B51) oxadiargyl,: 2) acetochlor, B53) metolachlor, B54) metosulam,: 5) oxyfluorfen, B56) dalapon, B57) metsulfuron,: 5) bensulfuron, B59) Pyrazosulfuron, B60) cmosulfuron, B61) imazosulfuron, B62) AC 322.140 (cyclosulfamuron), B63a) ethoxysulfuron (
  • a preferred use relates to the use of
  • Combinations that have levels of A and B compounds in a synergistically effective amount include:
  • the invention also includes mixtures with meh: as a combination partner A) and / or more than one combination partner B).
  • mixtures with meh as a combination partner A
  • combination partner B mixtures with meh
  • AI * + B19 anilofos + BIO Molmate AI u./o.
  • AI * + B19 anilofos + Bll thiobencarb AI u./o.
  • AI * + B19 anilofos + B12 pyributicarb AI u./o.
  • AI * + B19 anilofos + B13 quinclorac AI u./o.
  • AI u./o. AI * + B19 Anilofos + B17 Bayer NBA 061) AI u./o.
  • AI * + B19 anilofos + B18 piperophos AI u./o.
  • AI * + B19 anilofos + B24 dithiopyr AI u./o AI * + B19 anilofos + B25 bromobutide); AI u./o AI * + B19 Anilofos + B26 Cmmethylm); AI u./o AI * + B19 anilofos + B27 CH-900); AI u./o AI * + B19 anilofos + B28 2,4-D); AI u./o AI * + B19 Anilofos + B29 Mecoprop and / or Mecoprop-P); AI u./o. AI * + B19 anilofos + B30 MCPA); AI u./o.
  • AI u./o. AI * + B19 (Anilofos + B40 ((Triclopyr); AI u./o. AI * + B19 (Anilofos + B41 ((Benfuresate); AI u./o. AI * + B19 (Anilofos + B42 ((Daimuron) ; AI u./o. AI * + B19 (Anilofos + B43 ((Pendimethalin); AI u./o. AI * + B19 (Anilofos + B44 ((Clomazon);
  • AI u./o AI * + B19 anilofos + B46 ((pyrazolynate);
  • AI u./o AI * + B19 anilofos + B47 ((pyrazoxyfen);
  • AI u./o AI * + B19 Alofos + B57 ((Metsulfuron);
  • AI u./o AI * + B19 anilofos + B58 ((bensulfuron);
  • AI u./o AI * + B19 (Anilofos + B59 ((Pyrazosulfuron) AI u./o.
  • AI * + B19 (Anilofos + B60 ((Cinosulfuron);
  • AI * + B19 (Anilofos + B61 ((Imazosulfuron);
  • AI and / or AI * + B19 anilofos + B62 ((AC 322,140 (cyclosulfamuron));
  • AI u./o. AI * + B19 (Anilofos + B63a (Ethoxysulfuron (HOE 095404)) AI u./o. AI 1 B19 (Anilofos + B64 (Azimsulfuron (DPX- A8947)); AI u./o. AI * + B19 (Anilofos + B65 (nicosulfuron);
  • A3 + B19 (Anilofos + B5 (Mefenacet);
  • A3 + B19 (Anilofos + B6 (Naproanilide);
  • A2 u./o. A3 + B19 (Anilofos + BIO (Molinate); A2 u./o. A3 + B19 (Anilofos + Bll (Thiobencarb);
  • A2 u./o. A3 + B19 (Anilofos + B13 (Quinclorac); A2 u. /O. A3 + B19 anilofos + B14a sulcotrione);
  • B14a (Sulcotrione); AI u./o. AI * u./o. A2 u / o. A3 + B63a (ethoxysulfuron
  • A3 + B20 Fenoxaprop u./o, Fenoxaprop-P + B9 (Dimepiperate); AI u./o. AI * u./o. A2 u./o.
  • Fenoxaprop u./o Fenoxaprop-P + B12 (pyributicarb); AI u./o. AI * u./o. A2 u./o. A3 + B20 Tenoxaprop u./o. Fenoxaprop-P + B13 (Quinclorac); AI u./o. AI * u./o. A2 u./o. A3 + B20 [Fenoxaprop u./o, Fenoxaprop-P + Bl4a (Sulcotrione); AI u./o. AI * u./o. A2 u./o.
  • Fenoxaprop-P + B22 (DEH-112); AI u./o. AI * u./o. A2 u./o. A3 + B20 (Fenoxaprop u./o, Fenoxaprcp-P + B23 (JC-940); AI u./o. AI * u./o. A2 u./o. A3 + B20 Tenoxaprop u./o. Fenoxaprcp -P + B24 (dithiopyr); AI u./c. AI * u./o. A2 u./o.
  • A3 + B20 Fenoxaprop u./o. Fenoxaprop-P + B26 (Cinmethylin); I u./o. AI * u./o. A2 u./o.
  • A3 + B20 Fenoxaprop u./o. Fenoxaprop- P + B27 (CH-900); AI u./o. AI * u./o. A2 u./o.
  • A3 + B20 Fenoxaprop u./o.
  • Fenoxaprop-P + B31 (Dicamba); AI u./o. AI * u./o. A2 u./o.
  • A3 + B20 Fenoxaprop u./o. Fenoxaprop-P + B32 (Acifluorfen); AI u./o. AI * u./o. A2 u./o.
  • A3 + B20 Fenoxaprop u./o. Fenoxaprop-P + B33a and / or B33b; AI u ./o. AI * u./o. A2 u./o.
  • A3 + B20 Fenoxaprop u./o.
  • Fenoxaprop-P + B39 (Bentazon); AI u./o. AI * u./o. A2 u./o. A3 + B20 (Fenoxaprop u./o. Fenoxaprop-P + B40 (Triclopyr); AI u./o. AI * u./o. A2 u./o. A3 + B20 (Fenoxaprop u. / o. Fenoxaprop-P + B41 (Benfuresate); AI u./o. AI * u./o. A2 u./o. A3 + B20 (Fenoxaprop u./o. Fenoxaprop-P + B42 (daimuron); AI u./o.
  • A3 + B20 Fenoxaprop u./o. Fenoxaprop-P + B46 (Pyrazolynate); AI u./o. AI * u./o. A2 u. / o.
  • A3 + B20 Fenoxaprop u./o. Fenoxaprop-P + B47 (pyrazoxyfen); AI u./o. AI * u./o. A2 u./o.
  • A3 + B20 Fenoxaprop u./o. Fenoxaprop-P + B48 (KIH 2023); AI u./o. AI * u./o. A2 u./o.
  • A3 + B20 Fenoxaprop u./o.
  • Fenoxaprop-P B58 (bensulfuron); AI u./o. AI * u./o. A2 u./o. A3 + B20 (Fenoxaprop u./o.
  • Fenoxaprop-P B64 (azimsulfuron (DPX-A8947)); AI u./o. AI * u./o. A2 u./o. A3 + B20 (Fenoxaprop u./o.
  • mixtures described above with more than two components can expediently be used together with one or more safeners.
  • An example of a preferred safener is (5-chloro-8-quinolmoxy) acetic acid (1-methyl-hex-1-yl) ester (C2-1); the following mixtures result, for example:

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  • Life Sciences & Earth Sciences (AREA)
  • Dentistry (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Agronomy & Crop Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
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  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Peptides Or Proteins (AREA)

Abstract

L'invention concerne des herbicides, contenant (A) au moins un principe actif herbicide du groupe des phénylsulfonylurées substituées de la formule générale (I), et de leurs sels acceptés, c'est-à-dire acceptables pour l'usage agricole, formule dans laquelle R1 représente alkyle C¿1?-C8, alcényle C3-C4, alcynyle C3-C4 ou bien alkyle C1-C4, qui est substitué une à quatre fois par des radicaux du groupe halogène et/ou alcoxy C1-C2; R?2¿ représente I ou CH¿2?NHSO2CH3; R?3¿ est méthyle ou méthoxy; et Z est N ou bien CH; et (B) au moins un composé à action herbicide choisi dans le groupe des composés constitué (Ba) d'herbicides à action sélective chez le riz, principalement contre les graminées, (Bb) d'herbicides à action sélective chez le riz, principalement contre les plantes parasites dicotylédones et les cyperacées, (Bc) d'herbicides à action sélective chez le riz, principalement contre les cyperacées, et (Bd) d'herbicides à action sélective chez le riz, principalement contre les graminées et les plantes parasites dicotylédones ainsi que les cyperacées. Sont exclues de la revendication de substance les associations selon les brevets WO96/41537 et WO98/24320, lesdites associations exclues comportant, outre un ou plusieurs composés du type A, respectivement un seul principe actif du type B. Toutefois l'utilisation des associations de A et B connues d'après ces brevets WO pour lutter contre la croissance végétale parasite dans la riziculture n'est pas exclue de cette revendication de substance.
PCT/EP1999/004881 1998-07-16 1999-07-12 Herbicides a phenylsulfonylurees substituees pour lutter contre les mauvaises herbes chez le riz WO2000003597A1 (fr)

Priority Applications (15)

Application Number Priority Date Filing Date Title
MXPA01000572 MX224001B (es) 1998-07-16 1999-07-12 Agente herbicida con fenilsulfonilureas sustituidas para combatir las malas hierbas en el arroz.
KR20017000608A KR100676019B1 (ko) 1998-07-16 1999-07-12 벼에서 잡초를 방제하기 위한, 치환된 페닐설포닐우레아를함유한 제초 조성물
EP99936516A EP1096855B1 (fr) 1998-07-16 1999-07-12 Herbicides a phenylsulfonylurees substituees pour lutter contre les mauvaises herbes chez le riz
PL345665A PL198867B1 (pl) 1998-07-16 1999-07-12 Środki chwastobójcze, sposób ich wytwarzania i ich zastosowanie oraz sposób zwalczania niepożądanej roślinności
UA2001021086A UA70954C2 (uk) 1998-07-16 1999-07-12 Гербіцидний засіб і спосіб боротьби з небажаними рослинами
CA2337521A CA2337521C (fr) 1998-07-16 1999-07-12 Composition d'herbicides a phenylsulfonylurees substituees pour lutter contre les mauvaises herbes chez le riz
AU51587/99A AU769790B2 (en) 1998-07-16 1999-07-12 Herbicides with substituted phenylsulfonylureas for controlling weeds in rice
BRPI9912829-2A BR9912829B1 (pt) 1998-07-16 1999-07-12 composições herbicidas compreendendo fenilsulfoniluréias substituìdas, seu processo de preparação e seu uso, bem como método para o controle de plantas indesejáveis.
CN998102016A CN1314785B (zh) 1998-07-16 1999-07-12 用于防治稻田杂草的含有取代的苯基磺酰脲的除草组合物
HU0104456A HU229832B1 (en) 1998-07-16 1999-07-12 Herbicides with substituted phenylsulfonylureas for controlling weeds in rice plantation
DE59911002T DE59911002D1 (de) 1998-07-16 1999-07-12 Herbizide mittel mit substituierten phenylsulfonylharnstoffen zur unkrautbekämpfung in reis
JP2000559741A JP4621353B2 (ja) 1998-07-16 1999-07-12 イネの雑草を抑制するための置換フェニルスルホニル尿素含有除草剤組成物
IL14076599A IL140765A0 (en) 1998-07-16 1999-07-12 Herbicidal composition with substituted phenylsulfonylureas for controlling weeds in rice
AT99936516T ATE281077T1 (de) 1998-07-16 1999-07-12 Herbizide mittel mit substituierten phenylsulfonylharnstoffen zur unkrautbekämpfung in reis
SK52-2001A SK286315B6 (en) 1998-07-16 1999-07-12 Herbicidal compositions comprising substituted phenylsulfonylureas compounds for controlling weeds in rice, method for the preparation of the compositions and use thereof

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19832017.5 1998-07-16
DE19832017A DE19832017A1 (de) 1998-07-16 1998-07-16 Herbizide Mittel mit substituierten Phenylsulfonylharnstoffen zur Unkrautbekämpfung in Reis

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WO2000003597A1 true WO2000003597A1 (fr) 2000-01-27

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EP (1) EP1096855B1 (fr)
JP (1) JP4621353B2 (fr)
KR (1) KR100676019B1 (fr)
CN (2) CN1314785B (fr)
AR (1) AR019782A1 (fr)
AT (1) ATE281077T1 (fr)
AU (1) AU769790B2 (fr)
BG (1) BG65083B1 (fr)
BR (1) BR9912829B1 (fr)
CA (1) CA2337521C (fr)
CO (1) CO5221021A1 (fr)
CZ (1) CZ300185B6 (fr)
DE (2) DE19832017A1 (fr)
ES (1) ES2233061T3 (fr)
HU (1) HU229832B1 (fr)
ID (1) ID28899A (fr)
IL (1) IL140765A0 (fr)
MX (1) MX224001B (fr)
MY (1) MY126471A (fr)
PL (1) PL198867B1 (fr)
RU (1) RU2235466C2 (fr)
SK (1) SK286315B6 (fr)
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EP3954212A1 (fr) * 2015-07-10 2022-02-16 BASF Agro B.V. Procédé pour lutter contre les mauvaises herbes tolérantes ou résistantes aux herbicides, composition herbicide et procédé de lutte contre la végétation indésirable
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WO2003028466A2 (fr) * 2001-09-27 2003-04-10 Syngenta Participations Ag Composition herbicide
WO2003028466A3 (fr) * 2001-09-27 2003-10-30 Syngenta Participations Ag Composition herbicide
WO2003028460A3 (fr) * 2001-09-27 2003-10-30 Syngenta Participations Ag Composition herbicide
US7241720B2 (en) 2001-09-27 2007-07-10 Syngenta Crop Protection, Inc. Herbicidal composition
EA010053B1 (ru) * 2001-09-27 2008-06-30 Зингента Партисипейшнс Аг Гербицидная композиция
EP1315059A2 (fr) 2001-10-31 2003-05-28 Fluid Controls (UK) Limited Vanne de régulation de débit
CN102461549A (zh) * 2010-11-19 2012-05-23 南京华洲药业有限公司 一种含醚磺隆、二氯喹啉酸与氰氟草酯的混合除草剂及其应用
CN102461549B (zh) * 2010-11-19 2013-12-25 南京华洲药业有限公司 一种含醚磺隆、二氯喹啉酸与氰氟草酯的混合除草剂及其应用
CN103891747A (zh) * 2012-12-28 2014-07-02 青岛锦涟鑫商贸有限公司 一种改进的除草剂
EP3187049A1 (fr) * 2013-10-17 2017-07-05 Basf Se Composition herbicide comprenant l'inhibiteur d'acc cycloxydim

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